RU2014108140A - Соединение на основе хинозолина в качестве ингибиторов серен-треониновых киназ - Google Patents
Соединение на основе хинозолина в качестве ингибиторов серен-треониновых киназ Download PDFInfo
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- RU2014108140A RU2014108140A RU2014108140/04A RU2014108140A RU2014108140A RU 2014108140 A RU2014108140 A RU 2014108140A RU 2014108140/04 A RU2014108140/04 A RU 2014108140/04A RU 2014108140 A RU2014108140 A RU 2014108140A RU 2014108140 A RU2014108140 A RU 2014108140A
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- Prior art keywords
- methyl
- fluoro
- ylamino
- phenyl
- carboxamide
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- 108091000080 Phosphotransferase Proteins 0.000 title 1
- 239000004473 Threonine Substances 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 102000020233 phosphotransferase Human genes 0.000 title 1
- -1 2-oxabicyclo [2.2.1] heptan-5-yl Chemical group 0.000 claims abstract 178
- 150000001875 compounds Chemical class 0.000 claims abstract 26
- 229910052736 halogen Inorganic materials 0.000 claims abstract 10
- 150000002367 halogens Chemical class 0.000 claims abstract 10
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 5
- 125000003566 oxetanyl group Chemical group 0.000 claims abstract 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 3
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 3
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- 125000006300 thietan-3-yl group Chemical group [H]C1([H])SC([H])([H])C1([H])* 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 36
- TYHCBIKGTCZFTK-UHFFFAOYSA-N quinazoline-7-carboxamide Chemical compound C1=NC=NC2=CC(C(=O)N)=CC=C21 TYHCBIKGTCZFTK-UHFFFAOYSA-N 0.000 claims 19
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 5
- 150000001408 amides Chemical class 0.000 claims 5
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 4
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims 2
- AKRGWOSOKMUCSP-ZETCQYMHSA-N 2-[[(2s)-1-hydroxypropan-2-yl]amino]quinazoline-7-carboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=NC(N[C@H](CO)C)=NC=C21 AKRGWOSOKMUCSP-ZETCQYMHSA-N 0.000 claims 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- SYKRLDPZXIDMRJ-MBSDFSHPSA-N n-[(r)-(3-chloro-4-fluorophenyl)-[(3s)-pyrrolidin-3-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1[C@@H]([C@@H]1CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 SYKRLDPZXIDMRJ-MBSDFSHPSA-N 0.000 claims 2
- RCDKWQHFIJMQDJ-QHCPKHFHSA-N n-[(s)-(4-chloro-3-fluorophenyl)-(1-methylpyrazol-3-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound CN1C=CC([C@@H](NC(=O)C=2C=C3N=C(NC4CCOCC4)N=CC3=CC=2)C=2C=C(F)C(Cl)=CC=2)=N1 RCDKWQHFIJMQDJ-QHCPKHFHSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- NJNYEYUGBOCVCX-CMPLNLGQSA-N (R)-(3-fluoro-4-methoxyphenyl)-[(2S)-pyrrolidin-2-yl]methanamine Chemical compound COc1ccc(cc1F)[C@@H](N)[C@@H]1CCCN1 NJNYEYUGBOCVCX-CMPLNLGQSA-N 0.000 claims 1
- NWUZPNZUNARLLZ-LBPRGKRZSA-N (s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methanamine Chemical compound C1=C(F)C(OC)=CC=C1[C@H](N)C1=CN(C)N=C1 NWUZPNZUNARLLZ-LBPRGKRZSA-N 0.000 claims 1
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims 1
- NBXOSGJMUZEDBS-QFIPXVFZSA-N 2-(2-cyanoethylamino)-5-fluoro-n-[(s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methyl]quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C1=CN(C)N=C1)NC(=O)C1=CC(F)=C(C=NC(NCCC#N)=N2)C2=C1 NBXOSGJMUZEDBS-QFIPXVFZSA-N 0.000 claims 1
- WIVJYUYFVAZMMS-UHFFFAOYSA-N 2-(oxan-4-ylamino)quinazoline-7-carboxylic acid Chemical compound N=1C2=CC(C(=O)O)=CC=C2C=NC=1NC1CCOCC1 WIVJYUYFVAZMMS-UHFFFAOYSA-N 0.000 claims 1
- QYIZTCVUYUDJAX-DEOSSOPVSA-N 2-[(1,3-dimethylpyrazol-4-yl)amino]-5-fluoro-n-[(s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methyl]quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C1=CN(C)N=C1)NC(=O)C1=CC(F)=C(C=NC(NC=2C(=NN(C)C=2)C)=N2)C2=C1 QYIZTCVUYUDJAX-DEOSSOPVSA-N 0.000 claims 1
- KLXOIEADLOCBLO-OECQAKIHSA-N 2-[[(1R)-1-cyclopropylethyl]amino]-N-[(R)-(3-fluoro-4-methoxyphenyl)-[(2S)-pyrrolidin-2-yl]methyl]quinazoline-7-carboxamide Chemical compound FC=1C=C(C=CC1OC)[C@H]([C@H]1NCCC1)NC(=O)C1=CC=C2C=NC(=NC2=C1)N[C@H](C)C1CC1 KLXOIEADLOCBLO-OECQAKIHSA-N 0.000 claims 1
- UAAZNFCKBHKWRQ-QWRGUYRKSA-N 2-[[(3r,4s)-3-fluorooxan-4-yl]amino]quinazoline-7-carboxylic acid Chemical compound N=1C2=CC(C(=O)O)=CC=C2C=NC=1N[C@H]1CCOC[C@@H]1F UAAZNFCKBHKWRQ-QWRGUYRKSA-N 0.000 claims 1
- UAAZNFCKBHKWRQ-MNOVXSKESA-N 2-[[(3s,4s)-3-fluorooxan-4-yl]amino]quinazoline-7-carboxylic acid Chemical compound N=1C2=CC(C(=O)O)=CC=C2C=NC=1N[C@H]1CCOC[C@H]1F UAAZNFCKBHKWRQ-MNOVXSKESA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- VTPREKMEYVQFCQ-XUZZJYLKSA-N 5-fluoro-N-[(R)-(3-fluoro-4-methoxyphenyl)-[(2S)-pyrrolidin-2-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound FC=1C=C(C=CC1OC)[C@H]([C@H]1NCCC1)NC(=O)C1=CC(=C2C=NC(=NC2=C1)NC1CCOCC1)F VTPREKMEYVQFCQ-XUZZJYLKSA-N 0.000 claims 1
- KSKGTHMCOPFIGO-QFIPXVFZSA-N 5-fluoro-n-[(s)-(3-fluoro-4-methoxyphenyl)-(1-methylimidazol-2-yl)methyl]-2-[(2-methylpyrazol-3-yl)amino]quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C=1N(C=CN=1)C)NC(=O)C1=CC(F)=C(C=NC(NC=2N(N=CC=2)C)=N2)C2=C1 KSKGTHMCOPFIGO-QFIPXVFZSA-N 0.000 claims 1
- NGEZLEPIEDVAFP-DEOSSOPVSA-N 5-fluoro-n-[(s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C1=CN(C)N=C1)NC(=O)C1=CC(F)=C(C=NC(NC2CCOCC2)=N2)C2=C1 NGEZLEPIEDVAFP-DEOSSOPVSA-N 0.000 claims 1
- GRDYTJICKQLANR-QHCPKHFHSA-N 5-fluoro-n-[(s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methyl]-2-[(2-methylpyrazol-3-yl)amino]quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C1=CN(C)N=C1)NC(=O)C1=CC(F)=C(C=NC(NC=2N(N=CC=2)C)=N2)C2=C1 GRDYTJICKQLANR-QHCPKHFHSA-N 0.000 claims 1
- UEOXRBXYKVEYEB-HXOBKFHXSA-N 5-fluoro-n-[(s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(3r)-oxolan-3-yl]amino]quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C1=CN(C)N=C1)NC(=O)C1=CC(F)=C(C=NC(N[C@H]2COCC2)=N2)C2=C1 UEOXRBXYKVEYEB-HXOBKFHXSA-N 0.000 claims 1
- IWAVIKVCSQIPAX-QHCPKHFHSA-N 5-fluoro-n-[(s)-(3-fluoro-4-methoxyphenyl)-(3-methylimidazol-4-yl)methyl]-2-[(2-methylpyrazol-3-yl)amino]quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C=1N(C=NC=1)C)NC(=O)C1=CC(F)=C(C=NC(NC=2N(N=CC=2)C)=N2)C2=C1 IWAVIKVCSQIPAX-QHCPKHFHSA-N 0.000 claims 1
- VAAXWIOEAFXXOY-XMMPIXPASA-N ClC1=C(C=C(C=C1)[C@H](C1=NN(C=C1)CC)NC(=O)C1=CC=C2C=NC(=NC2=C1)NC1CCOCC1)F Chemical compound ClC1=C(C=C(C=C1)[C@H](C1=NN(C=C1)CC)NC(=O)C1=CC=C2C=NC(=NC2=C1)NC1CCOCC1)F VAAXWIOEAFXXOY-XMMPIXPASA-N 0.000 claims 1
- WNSYKSQGFKHXNC-QHCPKHFHSA-N FC(OC1=CC=C(C=C1)[C@@H](C=1C=NN(C1)C)NC(=O)C1=CC=C2C=NC(=NC2=C1)NC1CCOCC1)F Chemical compound FC(OC1=CC=C(C=C1)[C@@H](C=1C=NN(C1)C)NC(=O)C1=CC=C2C=NC(=NC2=C1)NC1CCOCC1)F WNSYKSQGFKHXNC-QHCPKHFHSA-N 0.000 claims 1
- XBGYKGMFTCOQNV-JTHBVZDNSA-N N-[(R)-(4-chloro-3-fluorophenyl)-[(2S)-pyrrolidin-2-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound ClC1=C(C=C(C=C1)[C@H]([C@H]1NCCC1)NC(=O)C1=CC=C2C=NC(=NC2=C1)NC1CCOCC1)F XBGYKGMFTCOQNV-JTHBVZDNSA-N 0.000 claims 1
- WPDRHVKUBYGIJD-JTHBVZDNSA-N N-[(R)-[3-fluoro-4-(trifluoromethyl)phenyl]-[(2S)-pyrrolidin-2-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound FC=1C=C(C=CC1C(F)(F)F)[C@H]([C@H]1NCCC1)NC(=O)C1=CC=C2C=NC(=NC2=C1)NC1CCOCC1 WPDRHVKUBYGIJD-JTHBVZDNSA-N 0.000 claims 1
- JYEXVJLIAPTLGM-PZJWPPBQSA-N N-[(R)-[3-fluoro-4-(trifluoromethyl)phenyl]-[(2S)-pyrrolidin-2-yl]methyl]-2-(propan-2-ylamino)quinazoline-7-carboxamide Chemical compound FC=1C=C(C=CC1C(F)(F)F)[C@H]([C@H]1NCCC1)NC(=O)C1=CC=C2C=NC(=NC2=C1)NC(C)C JYEXVJLIAPTLGM-PZJWPPBQSA-N 0.000 claims 1
- VAAXWIOEAFXXOY-DEOSSOPVSA-N N-[(S)-(4-chloro-3-fluorophenyl)-(1-ethylpyrazol-3-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound ClC1=C(C=C(C=C1)[C@@H](C1=NN(C=C1)CC)NC(=O)C1=CC=C2C=NC(=NC2=C1)NC1CCOCC1)F VAAXWIOEAFXXOY-DEOSSOPVSA-N 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000012634 fragment Substances 0.000 claims 1
- 230000003463 hyperproliferative effect Effects 0.000 claims 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- QSUJYAYZUAGHMC-UHFFFAOYSA-N n-[(3-chloro-4-fluorophenyl)-(3-fluoropyrrolidin-3-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1C(C1(F)CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 QSUJYAYZUAGHMC-UHFFFAOYSA-N 0.000 claims 1
- RCDKWQHFIJMQDJ-UHFFFAOYSA-N n-[(4-chloro-3-fluorophenyl)-(1-methylpyrazol-3-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound CN1C=CC(C(NC(=O)C=2C=C3N=C(NC4CCOCC4)N=CC3=CC=2)C=2C=C(F)C(Cl)=CC=2)=N1 RCDKWQHFIJMQDJ-UHFFFAOYSA-N 0.000 claims 1
- OZPDXPIOCLPNAM-UHFFFAOYSA-N n-[(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=NN(C)C=C1C(C=1C=C(F)C(Cl)=CC=1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 OZPDXPIOCLPNAM-UHFFFAOYSA-N 0.000 claims 1
- KJYWWRQXFYFUCA-JRTLGTJJSA-N n-[(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(2s)-1-hydroxypropan-2-yl]amino]quinazoline-7-carboxamide Chemical compound C=1C2=NC(N[C@H](CO)C)=NC=C2C=CC=1C(=O)NC(C=1C=C(F)C(Cl)=CC=1)C=1C=NN(C)C=1 KJYWWRQXFYFUCA-JRTLGTJJSA-N 0.000 claims 1
- SAXAAPPSFKUDQZ-UHFFFAOYSA-N n-[(4-chloro-3-fluorophenyl)-(3-fluoropyrrolidin-3-yl)methyl]-2-[(2-methylpyrazol-3-yl)amino]quinazoline-7-carboxamide Chemical compound CN1N=CC=C1NC1=NC=C(C=CC(=C2)C(=O)NC(C=3C=C(F)C(Cl)=CC=3)C3(F)CNCC3)C2=N1 SAXAAPPSFKUDQZ-UHFFFAOYSA-N 0.000 claims 1
- QSUJYAYZUAGHMC-RCZVLFRGSA-N n-[(r)-(3-chloro-4-fluorophenyl)-[(3r)-3-fluoropyrrolidin-3-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1[C@H]([C@]1(F)CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 QSUJYAYZUAGHMC-RCZVLFRGSA-N 0.000 claims 1
- QSUJYAYZUAGHMC-RDGATRHJSA-N n-[(r)-(3-chloro-4-fluorophenyl)-[(3s)-3-fluoropyrrolidin-3-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1[C@H]([C@@]1(F)CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 QSUJYAYZUAGHMC-RDGATRHJSA-N 0.000 claims 1
- OZPDXPIOCLPNAM-HSZRJFAPSA-N n-[(r)-(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=NN(C)C=C1[C@@H](C=1C=C(F)C(Cl)=CC=1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 OZPDXPIOCLPNAM-HSZRJFAPSA-N 0.000 claims 1
- HBBURBVOOIZAEO-XMMPIXPASA-N n-[(r)-(4-cyano-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=NN(C)C=C1[C@@H](C=1C=C(F)C(C#N)=CC=1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 HBBURBVOOIZAEO-XMMPIXPASA-N 0.000 claims 1
- QSUJYAYZUAGHMC-WIOPSUGQSA-N n-[(s)-(3-chloro-4-fluorophenyl)-[(3r)-3-fluoropyrrolidin-3-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1[C@@H]([C@]1(F)CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 QSUJYAYZUAGHMC-WIOPSUGQSA-N 0.000 claims 1
- SYKRLDPZXIDMRJ-WZONZLPQSA-N n-[(s)-(3-chloro-4-fluorophenyl)-[(3r)-pyrrolidin-3-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1[C@H]([C@H]1CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 SYKRLDPZXIDMRJ-WZONZLPQSA-N 0.000 claims 1
- QSUJYAYZUAGHMC-DHLKQENFSA-N n-[(s)-(3-chloro-4-fluorophenyl)-[(3s)-3-fluoropyrrolidin-3-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1[C@@H]([C@@]1(F)CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 QSUJYAYZUAGHMC-DHLKQENFSA-N 0.000 claims 1
- SYKRLDPZXIDMRJ-FDDCHVKYSA-N n-[(s)-(3-chloro-4-fluorophenyl)-[(3s)-pyrrolidin-3-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1[C@H]([C@@H]1CNCC1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 SYKRLDPZXIDMRJ-FDDCHVKYSA-N 0.000 claims 1
- LZHGVCWCMKIINY-DEOSSOPVSA-N n-[(s)-(3-chloro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(OC)=CC=C1[C@@H](C1=CN(C)N=C1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 LZHGVCWCMKIINY-DEOSSOPVSA-N 0.000 claims 1
- CBYWKDLUAXJBGF-DEOSSOPVSA-N n-[(s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C1=CN(C)N=C1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 CBYWKDLUAXJBGF-DEOSSOPVSA-N 0.000 claims 1
- JSJFGMIYPMMULT-QFIPXVFZSA-N n-[(s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methyl]-2-(thietan-3-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C1=CN(C)N=C1)NC(=O)C1=CC=C(C=NC(NC2CSC2)=N2)C2=C1 JSJFGMIYPMMULT-QFIPXVFZSA-N 0.000 claims 1
- VSSSIAXNZPSODL-CZSZKKDXSA-N n-[(s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(2s,4r)-2-(hydroxymethyl)oxan-4-yl]amino]quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H](C1=CN(C)N=C1)NC(=O)C1=CC=C(C=NC(N[C@H]2C[C@@H](CO)OCC2)=N2)C2=C1 VSSSIAXNZPSODL-CZSZKKDXSA-N 0.000 claims 1
- WEZUSONGOXQEOY-ANJVHQHFSA-N n-[(s)-(3-fluoro-4-methoxyphenyl)-[(2r,4s)-4-fluoropyrrolidin-2-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1[C@@H]([C@@H]1NC[C@@H](F)C1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 WEZUSONGOXQEOY-ANJVHQHFSA-N 0.000 claims 1
- OZPDXPIOCLPNAM-QHCPKHFHSA-N n-[(s)-(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=NN(C)C=C1[C@H](C=1C=C(F)C(Cl)=CC=1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 OZPDXPIOCLPNAM-QHCPKHFHSA-N 0.000 claims 1
- KAVNWTJUHVNYDE-QFIPXVFZSA-N n-[(s)-(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-[(2-methylpyrazol-3-yl)amino]quinazoline-7-carboxamide Chemical compound C1=NN(C)C=C1[C@H](C=1C=C(F)C(Cl)=CC=1)NC(=O)C1=CC=C(C=NC(NC=2N(N=CC=2)C)=N2)C2=C1 KAVNWTJUHVNYDE-QFIPXVFZSA-N 0.000 claims 1
- FWSWGJRTWXRQJN-SKPFHBQLSA-N n-[(s)-(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(2s,4s)-2-(hydroxymethyl)oxan-4-yl]amino]quinazoline-7-carboxamide Chemical compound C1=NN(C)C=C1[C@H](C=1C=C(F)C(Cl)=CC=1)NC(=O)C1=CC=C(C=NC(N[C@@H]2C[C@@H](CO)OCC2)=N2)C2=C1 FWSWGJRTWXRQJN-SKPFHBQLSA-N 0.000 claims 1
- RYAVEUFXJVCQNW-XJUOHMSHSA-N n-[(s)-(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2-[[(3r,4r)-3-fluorooxan-4-yl]amino]quinazoline-7-carboxamide Chemical compound C1=NN(C)C=C1[C@H](C=1C=C(F)C(Cl)=CC=1)NC(=O)C1=CC=C(C=NC(N[C@H]2[C@H](COCC2)F)=N2)C2=C1 RYAVEUFXJVCQNW-XJUOHMSHSA-N 0.000 claims 1
- BJQJOYNOELTEHJ-CHVDNLQBSA-N n-[(s)-(4-chloro-3-fluorophenyl)-[(2r,5r)-5-methylpyrrolidin-2-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound N1[C@H](C)CC[C@@H]1[C@H](C=1C=C(F)C(Cl)=CC=1)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 BJQJOYNOELTEHJ-CHVDNLQBSA-N 0.000 claims 1
- IOOCGMZCMZXLSH-OPURJYLOSA-N n-[(s)-(4-chloro-3-fluorophenyl)-[(2s)-pyrrolidin-2-yl]methyl]-2-[[(2s)-1,1,1-trifluoropropan-2-yl]amino]quinazoline-7-carboxamide Chemical compound C([C@H]1[C@@H](NC(=O)C=2C=CC3=CN=C(N=C3C=2)N[C@@H](C)C(F)(F)F)C=2C=C(F)C(Cl)=CC=2)CCN1 IOOCGMZCMZXLSH-OPURJYLOSA-N 0.000 claims 1
- ILXGLHJWTMZTDE-RPWUZVMVSA-N n-[(s)-[3-fluoro-4-(trifluoromethyl)phenyl]-[(2r)-1-methylpyrrolidin-2-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound CN1CCC[C@@H]1[C@H](C=1C=C(F)C(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(C=NC(NC2CCOCC2)=N2)C2=C1 ILXGLHJWTMZTDE-RPWUZVMVSA-N 0.000 claims 1
- WPDRHVKUBYGIJD-GMAHTHKFSA-N n-[(s)-[3-fluoro-4-(trifluoromethyl)phenyl]-[(2s)-pyrrolidin-2-yl]methyl]-2-(oxan-4-ylamino)quinazoline-7-carboxamide Chemical compound C1=C(C(F)(F)F)C(F)=CC([C@H](NC(=O)C=2C=C3N=C(NC4CCOCC4)N=CC3=CC=2)[C@H]2NCCC2)=C1 WPDRHVKUBYGIJD-GMAHTHKFSA-N 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161515165P | 2011-08-04 | 2011-08-04 | |
| US61/515,165 | 2011-08-04 | ||
| PCT/US2012/049551 WO2013020062A1 (en) | 2011-08-04 | 2012-08-03 | Quinazoline compounds as serine/threonine kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2014108140A true RU2014108140A (ru) | 2015-09-10 |
Family
ID=47003195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014108140/04A RU2014108140A (ru) | 2011-08-04 | 2012-08-03 | Соединение на основе хинозолина в качестве ингибиторов серен-треониновых киназ |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9187462B2 (enExample) |
| EP (1) | EP2739618B1 (enExample) |
| JP (1) | JP6097289B2 (enExample) |
| KR (1) | KR101979042B1 (enExample) |
| CN (1) | CN103958502B (enExample) |
| BR (1) | BR112014002675A2 (enExample) |
| CA (1) | CA2844058A1 (enExample) |
| ES (1) | ES2552989T3 (enExample) |
| MX (1) | MX340756B (enExample) |
| RU (1) | RU2014108140A (enExample) |
| WO (1) | WO2013020062A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US9133187B2 (en) | 2011-02-28 | 2015-09-15 | Array Biopharma Inc. | Serine/threonine kinase inhibitors |
| ES2552989T3 (es) | 2011-08-04 | 2015-12-03 | Array Biopharma, Inc. | Compuestos de quinazolina como inhibidores de la cinasa de serina / treonina |
| PE20150666A1 (es) | 2012-03-01 | 2015-05-06 | Array Biopharma Inc | Inhibidores de serina/treonina cinasa |
| CA2882750A1 (en) * | 2012-08-27 | 2014-03-06 | Jim Blake | Serine/threonine kinase inhibitors for the treatment of hyperproliferative|diseases |
| EP2909206A1 (en) | 2012-10-16 | 2015-08-26 | F. Hoffmann-La Roche AG | Serine/threonine kinase inhibitors |
| CN103254142B (zh) * | 2013-04-26 | 2015-10-28 | 浙江工业大学 | 4-[4-(2-取代氨基乙酰氨基)苯胺基]喹唑啉类衍生物及制备和应用 |
| US9532987B2 (en) | 2013-09-05 | 2017-01-03 | Genentech, Inc. | Use of a combination of a MEK inhibitor and an ERK inhibitor for treatment of hyperproliferative diseases |
| EA031243B1 (ru) | 2013-12-06 | 2018-12-28 | Дженентек, Инк. | Ингибиторы серин/треонинкиназ |
| MX375902B (es) | 2013-12-30 | 2025-03-07 | Genentech Inc | Inhibidores de serina/treonina cinasa. |
| KR102379517B1 (ko) * | 2013-12-30 | 2022-03-25 | 제넨테크, 인크. | 세린/트레오닌 키나아제 억제제 |
| KR102359214B1 (ko) | 2014-04-04 | 2022-02-07 | 델 마 파마슈티컬스 | 폐의 비소세포 암종 및 난소암을 치료하기 위한 디안하이드로갈락티톨 및 이의 유사체 또는 유도체 |
| AU2017249229A1 (en) | 2016-04-15 | 2018-10-04 | Genentech, Inc. | Diagnostic and therapeutic methods for cancer |
| KR102811888B1 (ko) | 2017-09-08 | 2025-05-27 | 에프. 호프만-라 로슈 아게 | 암의 진단 및 치료 방법 |
| US20210008047A1 (en) | 2018-02-13 | 2021-01-14 | Vib Vzw | Targeting minimal residual disease in cancer with rxr antagonists |
| WO2019213403A1 (en) | 2018-05-02 | 2019-11-07 | Kinnate Biopharma Inc. | Inhibitors of cyclin-dependent kinases |
| SG11202013175SA (en) | 2018-06-29 | 2021-01-28 | Kinnate Biopharma Inc | Inhibitors of cyclin-dependent kinases |
| EP4371987B9 (en) | 2018-10-31 | 2025-11-26 | Gilead Sciences, Inc. | Substituted 6-azabenzimidazole compounds as hpk1 inhibitors |
| EP3873608A1 (en) | 2018-10-31 | 2021-09-08 | Gilead Sciences, Inc. | Substituted 6-azabenzimidazole compounds having hpk1 inhibitory activity |
| US11453681B2 (en) | 2019-05-23 | 2022-09-27 | Gilead Sciences, Inc. | Substituted eneoxindoles and uses thereof |
| CN115243687A (zh) | 2019-10-25 | 2022-10-25 | 默沙东有限责任公司 | 作为lrrk2抑制剂的n-(杂芳基)喹唑啉-2-胺衍生物、药物组合物及其用途 |
| CN115448864B (zh) * | 2022-08-26 | 2023-12-22 | 上海方予健康医药科技有限公司 | 3-氟-3-（1-羟乙基）吡咯烷-1-羧酸叔丁酯的制备方法 |
Family Cites Families (36)
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| AU693475B2 (en) | 1993-10-01 | 1998-07-02 | Novartis Ag | Pyrimidineamine derivatives and processes for the preparation thereof |
| PT672042E (pt) | 1993-10-01 | 2006-08-31 | Novartis Ag | Derivados de pirimidinoamina farmacologicamente activos e processos para a sua preparacao |
| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
| CA2274093C (en) | 1996-12-05 | 2006-11-07 | Amgen Inc. | Substituted pyrimidinone and pyridinone compounds and their use |
| US6602872B1 (en) | 1999-12-13 | 2003-08-05 | Merck & Co., Inc. | Substituted pyridazines having cytokine inhibitory activity |
| YU63802A (sh) | 2000-02-25 | 2005-06-10 | F. Hoffmann-La Roche Ag. | Modulatori adenozinskih receptora |
| AU2001252606B2 (en) | 2000-04-26 | 2005-07-07 | Eisai R&D Management Co., Ltd. | Medicinal compositions promoting bowel movement |
| WO2002088079A2 (en) | 2001-05-01 | 2002-11-07 | Bristol-Myers Squibb Company | Dual inhibitors of pde 7 and pde 4 |
| WO2003030909A1 (en) | 2001-09-25 | 2003-04-17 | Bayer Pharmaceuticals Corporation | 2- and 4-aminopyrimidines n-substtituded by a bicyclic ring for use as kinase inhibitors in the treatment of cancer |
| MXPA04011470A (es) | 2002-05-21 | 2005-02-14 | Amgen Inc | Compuestos heterociclicos sustituidos y metodos de uso. |
| WO2004007468A1 (en) | 2002-07-15 | 2004-01-22 | Merck & Co., Inc. | Piperidino pyrimidine dipeptidyl peptidase inhibitors for the treatment of diabetes |
| TW200533357A (en) | 2004-01-08 | 2005-10-16 | Millennium Pharm Inc | 2-(amino-substituted)-4-aryl pyrimidines and related compounds useful for treating inflammatory diseases |
| KR100799802B1 (ko) * | 2004-02-04 | 2008-01-31 | 화이자 프로덕츠 인크. | 치환된 퀴놀린 화합물 |
| JP2007532669A (ja) | 2004-04-13 | 2007-11-15 | イカジェン インコーポレイテッド | カリウムイオンチャネル調節剤としての多環式ピリミジン |
| US7429604B2 (en) | 2004-06-15 | 2008-09-30 | Bristol Myers Squibb Company | Six-membered heterocycles useful as serine protease inhibitors |
| CA2578122A1 (en) | 2004-08-27 | 2006-03-02 | Gpc Biotech Ag | Pyrimidine derivatives |
| GB0420722D0 (en) | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| GB0428514D0 (en) | 2004-12-31 | 2005-02-09 | Prosidion Ltd | Compounds |
| EP1871762A2 (en) | 2005-04-18 | 2008-01-02 | Neurogen Corporation | Subtituted heteroaryl cb1 antagonists |
| US7572809B2 (en) | 2005-12-19 | 2009-08-11 | Hoffmann-La Roche Inc. | Isoquinoline aminopyrazole derivatives |
| JP2009528280A (ja) | 2006-02-16 | 2009-08-06 | シェーリング コーポレイション | Ｅｒｋインヒビターとしてのピロリジン誘導体 |
| WO2007125405A2 (en) | 2006-05-01 | 2007-11-08 | Pfizer Products Inc. | Substituted 2-amino-fused heterocyclic compounds |
| DE102006035202A1 (de) | 2006-07-29 | 2008-01-31 | Lanxess Deutschland Gmbh | Konservierungsmittel auf Basis von Carbonsäureanhydriden |
| CA2661334C (en) | 2006-08-23 | 2011-11-29 | Pfizer Products Inc. | Pyrimidone compounds as gsk-3 inhibitors |
| WO2008039882A1 (en) | 2006-09-30 | 2008-04-03 | Sanofi-Aventis U.S. Llc | A combination of niacin and a prostaglandin d2 receptor antagonist |
| EP2094682A2 (en) | 2006-12-22 | 2009-09-02 | Novartis AG | Heteroaryl-heteroaryl compounds as cdk inhibitors for the treatment of cancer, inflammation and viral infections |
| EP2200436B1 (en) | 2007-09-04 | 2015-01-21 | The Scripps Research Institute | Substituted pyrimidinyl-amines as protein kinase inhibitors |
| MX2010005033A (es) | 2007-11-06 | 2010-05-27 | Du Pont | Aminas heterociclicas fungicidas. |
| WO2009146034A2 (en) * | 2008-03-31 | 2009-12-03 | Takeda Pharmaceutical Company Limited | Mapk/erk kinase inhibitors and methods of use thereof |
| AU2009262068C1 (en) | 2008-06-27 | 2015-07-02 | Celgene Car Llc | Heteroaryl compounds and uses thereof |
| WO2009156484A2 (en) | 2008-06-27 | 2009-12-30 | Novartis Ag | Organic compounds |
| PT2370413E (pt) | 2008-12-08 | 2015-10-23 | Arena Pharm Inc | Moduladores do recetor da prostaciclina (pgi2) úteis para o tratamento de distúrbios relacionados com o mesmo |
| US9133187B2 (en) | 2011-02-28 | 2015-09-15 | Array Biopharma Inc. | Serine/threonine kinase inhibitors |
| ES2552989T3 (es) | 2011-08-04 | 2015-12-03 | Array Biopharma, Inc. | Compuestos de quinazolina como inhibidores de la cinasa de serina / treonina |
| PE20150666A1 (es) | 2012-03-01 | 2015-05-06 | Array Biopharma Inc | Inhibidores de serina/treonina cinasa |
| CA2882750A1 (en) | 2012-08-27 | 2014-03-06 | Jim Blake | Serine/threonine kinase inhibitors for the treatment of hyperproliferative|diseases |
-
2012
- 2012-08-03 ES ES12769775.3T patent/ES2552989T3/es active Active
- 2012-08-03 MX MX2014001389A patent/MX340756B/es active IP Right Grant
- 2012-08-03 JP JP2014524111A patent/JP6097289B2/ja active Active
- 2012-08-03 WO PCT/US2012/049551 patent/WO2013020062A1/en not_active Ceased
- 2012-08-03 CA CA2844058A patent/CA2844058A1/en not_active Abandoned
- 2012-08-03 EP EP12769775.3A patent/EP2739618B1/en active Active
- 2012-08-03 US US14/237,143 patent/US9187462B2/en active Active
- 2012-08-03 KR KR1020147005731A patent/KR101979042B1/ko not_active Expired - Fee Related
- 2012-08-03 BR BR112014002675A patent/BR112014002675A2/pt not_active IP Right Cessation
- 2012-08-03 CN CN201280049268.3A patent/CN103958502B/zh active Active
- 2012-08-03 RU RU2014108140/04A patent/RU2014108140A/ru not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP2739618B1 (en) | 2015-09-16 |
| KR101979042B1 (ko) | 2019-05-15 |
| HK1199248A1 (zh) | 2015-06-26 |
| ES2552989T3 (es) | 2015-12-03 |
| US9187462B2 (en) | 2015-11-17 |
| JP2014521696A (ja) | 2014-08-28 |
| CN103958502A (zh) | 2014-07-30 |
| JP6097289B2 (ja) | 2017-03-15 |
| WO2013020062A1 (en) | 2013-02-07 |
| US20150087664A1 (en) | 2015-03-26 |
| EP2739618A1 (en) | 2014-06-11 |
| HK1199021A1 (zh) | 2015-06-19 |
| BR112014002675A2 (pt) | 2017-02-21 |
| MX340756B (es) | 2016-07-25 |
| MX2014001389A (es) | 2014-11-13 |
| KR20140062057A (ko) | 2014-05-22 |
| CN103958502B (zh) | 2016-02-10 |
| CA2844058A1 (en) | 2013-02-07 |
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